Darren J Ray is an entertainer whose regular club and RSL gigs bring a lot of joy to his devoted fans.

However joy went out the window when his relationship with much younger ex-girlfriend Belinda Hope ended.

Instead began one of the most bizarre civil legal battles we've ever seen.

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Ray believes he's out of pocket to the tune of $421.47 - money spent during his four or five year relationship with Hope, who was some eighteen years his junior.

Ray says his first loan to Hope was for $100. "She was a student, I was an entertainer and it was a case of her dog having to go to the vet and she loves her dogs, so you know you're not going to say no," he said.

On top of the money Ray claims was loaned for vet bills he wants $171.47 that he paid for a ticket to the Splendour in the Grass music festival.

"That was a loan. You know when somebody says to you 'oh baby can you loan me some money I'll pay you back' - that is a loan," Ray said.

But when you enter a relationship, or when you're in love, is a loan still a loan?

According to Ray it very much is. "I always I knew .. that I would be repaid, you know, you believe somebody. When it came to the realisation that it was going to be a fight, it was just sad you know"

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Ray is also pursuing Hope through the Queensland Civil and Administrative Tribunal for $100 in cash for petrol money.

"There were instances we'd be driving around Tweed (and she'd say) 'Oh i need some petrol. Oh I haven't got any money, can you loan me $20, or can you pay for my petrol, I'll pay you back'," Ray recalled.

What's driving him now, he says, is the principle of the matter, and that's why he is also demanding Hope repay him $50 for a dog blanket he bought her.

"She wanted a quilt to put on the bed because the dogs would get dirty, and she didn't want her bed to get dirty. She sleeps with her dogs so she asked me if I would be on the lookout and get her a queen size quilt," Ray said.

Since the money has been owing for close to a decade Ray is also seeking an interest payment of $254.30 as well as $28 from Hope's mother for alcohol and cigarettes.

When we contacted Hope she declined to comment, preferring to let sleeping dogs lie.

Ray's advice to other men is that "you can lose in love but just don't loan money, or if you do make sure you get it in writing."

In dismissing Ray's claim, and later his appeal, the Queensland Civil and Administrative Tribunal found what's loaned in love isn't necessarily a binding contract that's enforceable by a court.

This reporter is on Twitter at @DamienHansen7